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ledaborbactam   Click here for help

GtoPdb Ligand ID: 13082

Synonyms: VNRX-5236
Compound class: Synthetic organic
Comment: Ledaborbactam (VNRX-5236) is a novel broad-spectrum boronic acid β-lactamase inhibitor (BLI). It is a reversible covalent inhibitor of serine β-lactamases (classes A, C, D) [1].
Ledaborbactam etzadroxil (VNRX-7145, PubChem CID 138455030), an orally bioavailable prodrug of ledaborbactam [3], is being developed in combination with ceftibuten for the treatment of infections caused by drug-resistant Enterobacterales.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 95.86
Molecular weight 263.05
XLogP 0.49
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCC(=O)N[C@H]1CC2=CC=CC(=C2OB1O)C(=O)O
Isomeric SMILES B1([C@H](CC2=C(O1)C(=CC=C2)C(=O)O)NC(=O)CC)O
InChI InChI=1S/C12H14BNO5/c1-2-10(15)14-9-6-7-4-3-5-8(12(16)17)11(7)19-13(9)18/h3-5,9,18H,2,6H2,1H3,(H,14,15)(H,16,17)/t9-/m0/s1
InChI Key QAGGLFCWUVSERJ-VIFPVBQESA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(3R)-2-hydroxy-3-(propanoylamino)-3,4-dihydro-1,2-benzoxaborinine-8-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
11708 ledaborbactam
Synonyms Click here for help
VNRX-5236
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Ledaborbactam
Other databases
CAS Registry No. 1842397-36-7 (source: Scifinder)
ChEMBL Ligand CHEMBL5093566
GtoPdb PubChem SID 491299864
PubChem CID 138455079
Search Google for chemical match using the InChIKey QAGGLFCWUVSERJ-VIFPVBQESA-N
Search Google for chemicals with the same backbone QAGGLFCWUVSERJ
Search PubMed clinical trials ledaborbactam
Search PubMed titles ledaborbactam
Search PubMed titles/abstracts ledaborbactam
UniChem Compound Search for chemical match using the InChIKey QAGGLFCWUVSERJ-VIFPVBQESA-N
UniChem Connectivity Search for chemical match using the InChIKey QAGGLFCWUVSERJ-VIFPVBQESA-N